3 Challenges You'll Face When Scaling Your Startup Team

We’re facing a small challenge at the HelloSign office. Need a hint? It’s bigger than a breadbox and smaller than a gymnasium.

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I’m talking about our office space.

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Over the last few months, we’ve added to our team at a rapid pace. At the beginning of 2014, we were a lean team of under 15 employees. Since then, we’ve more than doubled the number and moved our office location to fit all the new faces.

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Growing the team is just one way we’re leveling up as a company. That said, the team scale has also led us to face some common challenges that result from adding more brains to an operation.

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And because we know firsthand how tricky it can be to maintain balance and momentum when adding to a team, we wanted to share some of the “lessons learned” during our own team scale.

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Here are 3 common challenges companies face when scaling a team, and how the HelloSign team members and Team Ops have worked to overcome them:

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Challenge # 1: Physical Space

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We’ll start off with the most obvious logistical challenge: physical space.

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Matching office size with team size will always pose a challenge for the scaling company or startup. Too large and the space feels empty. Too small and the space feels cramped.

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And while finding the purrfectly sized (couldn’t help it) space may always seem top of mind when picking out a location, environment can have a big impact on employee morale. With average full-time employees spending upwards of 40 hours a week in the office space, curating a comfortable and workable environment is critical.

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As HelloSign has grown, we’ve taken proactive measures to make sure our office space remains a comfortable working environment for HS employees.

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Here are a few examples of how to approach the space challenge:

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Optimized desk groupings for space and communication. To optimize the space we do have, we’ve been intentional and deliberate in how we organize the desk structure. That’s right: desk Tetris.

Not only does optimizing desk groupings help keep the office organized, it’s also an opportunity to mix up teams. Marketing has been joined by 2 engineers and the support team is mixed with the sales team. Cross-team grouping represents the collaborative company structure and it has the benefit of organizing open desk spaces effectively.

Continued to be transparent when reevaluating communal spaces. We’re fortunate to have excellent communal spaces in the HelloSign office. We have several areas to escape from the monitors and a shared lunch area which is conveniently located smack dab in the middle of our office.

But as we consider how to welcome new people onto our team, we’ve come up against a hard question: how do we prioritize this extra open space? Further, how do we reevaluate shared communal areas? As we continue to scale, we recognize that every change can be felt by the team, even small layout changes. Before any changes are made, they’re evaluated and then announced to the team. This loops in team members to potential changes and prepares the team for adjustments.

Revamped how we book and utilize our meeting spaces. Meeting rooms are one of the most prized properties in the office. We value having rooms to check in across teams without disturbing others. One way we’ve approached the meeting space challenge is to trim down our default meeting time from 60 min -> 30 minutes. The small switch keeps us mindful of how we book space and remain cognizant about our meeting habits.

Experimenting with walking meetings (when possible) has been another way that we’ve iterated. We’re also in the process of prioritizing one of our conference rooms for recruiting & interviews. The remaining rooms are being optimized for space and scheduling.

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In addition to these current “in-action” changes, preparation for future growth is also a big part of our process. This includes keeping an open conversation with the current building manager, staying in tune with the speed of growth and future headcount, and keeping an ear to the ground for new potential office spaces.

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Challenge # 2: Scaling Internal Systems

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We have something pretty magical going on at HelloSign: we all know everyone’s name. As we continue to develop our inter-team infrastructure, we currently have the luxury to do so in one room.

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But as we grow we know that systems that worked for a leaner team may not always translate to a larger team. To remain relevant to the growing size of our company, we’re in constant feedback gathering mode.

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Feedback has always been an integral part of our infrastructure. But it’s particularly important as we continue to scale. Adding to the team provides the opportunity to evaluate our internal team structures on a rolling basis. When new systems don’t work, we assess and gather feedback before tweaking and editing as necessary. We accomplish this using various feedback loops.

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For example, we recently set up a system for sharing feedback or suggestions with our CEO, Joseph Walla. The feedback system is based on a standard suggestion box model, making it easy to anonymously send thoughts and feedback. While it’s not the end all be all solution, we know it’s just one way to experiment with communication and feedback. We’ll continue to iterate and tweak as necessary (and have already done so by experimenting with Office Hours and experimenting with our team meeting structure).

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The most important thing to remember: taking action on these steps and measuring success as you iterate is just as crucial as planning them out.

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Challenge # 3: Team Silos and Cross-Team Communication

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When you start out with a small team, you’re likely more focused on keeping fires at bay as opposed to thinking about which specific department (or individual) is responsible for responding to the fire. You can shout “All hands on deck!” and the call will be heard. But as you scale and begin to build out specialized teams, it’s easy for individuals to lose that sense of cross-team involvement.

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Suddenly, each member is manning a dinghy instead of working together to sail the bigger ship.

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As you continue to scale your company, it’s common that you’ll encounter the issue of team exclusivity or working silos.

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Then, you know how it goes. Marketing only eats with marketing. Engineering only eats with engineering. Departments stick together, right? Not if you remain proactive.

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Offering opportunities for interaction between teams (whether via extracurricular activities or through company goals) has been key in creating and supporting a climate of collaboration. From the first day of onboarding up to the last minute on a Friday afternoon, questions are encouraged and supported at HelloSign.
Our Team Ops lead Gina Lau shared a few examples of how we manage to keep teams connected:

Regularly hosted team lunches as a method to unite the team outside of projects and encourage casual rapport. “Friday team lunches have been essential in fostering casual interaction & unplanned rapport building.”

A company-wide chat channel to connect employees. “We always send a blast in Hipchat to see who wants to grab lunch together. Anyone is invited.”

Prioritizing casual opportunities for connection. “Social connectors like birthday celebrations, release parties (we held one for our UI redesign), monthly photo walks through the city, and all of our coffee experts have contributed to this collaboration.”

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Additionally, Gina shared some examples of how active transparency has addressed the potential for team silos:

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“Another way we combat team silos is with active transparency. The more context everyone has about other departments, the more we feel like one cohesive unit.

For example, different team members present interesting and relevant information at our weekly team meetings. We'll have newer sales reps talk about their most recent big sales, engineers will demo interesting ways customers have integrated our e-signature API, our marketing designer presents the design collateral she's produced to reinforce our company values.”

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Deliberate steps like these (and continued iterations) have been key in building out the office and maintain balance as new members are added.

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Growing a team is an ongoing project, but proactivity = less pain

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Each time we add a new employee to the team, we learn from the experience. And trust us, we’ve learned a lot. But one thing remains the same: what you do with the experience is where the success lies.

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As mentioned, gathering and assessing feedback gives us the insight needed to react to potential issues. Ultimately, it’s a critical piece that informs how we approach our company goals and initiatives.

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As we continue adding to our team, we’re excited to keep innovating and creating a foundation to support new team members.